3-{4-[6-(1-Hydroxymethyl-propylamino)-2-oxo-3-propyl-3,7-dihydro2H-purin-8-yl]-bicyclo[2.2.2]oct-1-yl]-propionic acid methyl ester → HCID 178456576, Verbindung
Reaktionsgleichung
C[O:2][C:3](=[O:33])[CH2:4][CH2:5][C:6]12[CH2:13][CH2:12][C:9]([C:14]3[NH:22][C:21]4[C:20]([NH:23][CH:24]([CH2:27]O)[CH2:25][CH3:26])=[N:19][C:18](=[O:29])[N:17]([CH2:30][CH2:31][CH3:32])[C:16]=4[N:15]=3)([CH2:10][CH2:11]1)[CH2:8][CH2:7]2>O=S(Cl)Cl>[CH2:25]([CH:24]1[N:23]=[C:20]2[N:19]([C:18](=[O:29])[N:17]([CH2:30][CH2:31][CH3:32])[C:16]3[N:15]=[C:14]([C:9]45[CH2:12][CH2:13][C:6]([CH2:5][CH2:4][C:3]([OH:2])=[O:33])([CH2:7][CH2:8]4)[CH2:11][CH2:10]5)[NH:22][C:21]=32)[CH2:27]1)[CH3:26]Komponenten
3
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
3-{4-[6-(1-Hydroxymethyl-propylamino)-2-oxo-3-propyl-3,7-dihydro-2H-purin-8-yl]-bicyclo[2.2.2]oct-1-yl}-propionic acid methyl ester (30 mg) was dissolved in 1 mL of SOCl2 and stirred under reflux for 15 min. The reaction mixture was then cooled to rt and concentrated under reduced pressure. The resulting residue was dissolved in a solution containing 1 mL of water, 0.5 mL of MeOH, and 0.1 mL of 10% aq. NaOH. The reaction mixture was stirred at rt for 30 min. It was then acidified to pH 2 with dilute 1 N HCl and concentrated. The resulting crude product was purified by preparative HPLC to afford the titled compound.